He grew up in Highland Park before moving to Potomac, Maryland, when he was in ninth grade. He attended Bullis School. He passed for 5,308 yards and 54 touchdowns in Bullis. After high school, he promised to play college football at the University of Maryland.
The Washington Redskins selected him in the first round with the 15th overall pick in the 2019 NFL Draft. The Redskins had unofficially removed shirt number 7 in the 1980s in honor of quarterback Joe Theismann. Haskins requested number 7 and was granted.